Learning to (Let Myself) Flirt Again

Last night I had a dream where I felt erotic electricity with a stranger, and I was having so much fun flirting with him while shopping at Costco. When it was time to check out, I was flushed with grief—grief, and guilt.

“What’s the guilt about?” A friend of mine asked. “Do you like this guy more than Misha?”

“Pshhht! No. No way. Misha is a genius, the smartest man I’ve ever met. He has a way of talking to people with a piercing curiosity that opens them up in ways that feel like magic. I’m in awe of him. He’s so funny and clever, and I can’t imagine a better person for me. No. That’s not it.”

“What is it then?”

I thought about the Tom Cruise looking fellow I’d been flirting with all afternoon, anticipating his remorse when I told him I was married, and that although I felt electricity with him, and had so much fun with him, this would be the end. I anticipated his shaming; him telling me I led him on.

“I feel guilty for flirting, as if I’ve betrayed both Misha and this guy.”

“But you are a flirty person! That’s just who you are. You’re allowed to have fun.”

When I woke up, I talked to Misha who also assured me that I had nothing to feel guilty about, but I still couldn’t shake it. I was brought back to high school and college, when my college boyfriend implied having any kind of interaction with other guys was a hurtful, intentional crime. There was only one period in my life where I flirted recklessly without shame, a time I look back on with rosy glasses for the independent, confident young woman I was—the one year between my high school boyfriend and committing to Misha.

During that time, I felt I was seeing the world clearly. People would laugh too hard at my jokes, and I could see it was because they wanted to fuck me. Men would give me more time and energy than my stature should warrant, but I had fun flirting and enjoying their company anyway. I dropped the veil of delusion that protected me during my early relationship and got to relish the sexual attention of others, giving me confidence and joie de vivre I carried with me everywhere.

Now that we are in the Lifestyle, I know it’s okay to flirt again, part of the point is to enjoy that sexual attention again and let it fuel and drive my passion for life and my lover, but I can tell I’m still holding back. When we go to a club, I don’t feel that same confidence I used to carry, despite being much hotter and more secure in myself now. I know, intellectually, that people are interested in me (and us), but I have a hard time letting myself experience it. As a result, flirting isn’t the same fun it used to be—I don’t feel that ease of knowing I’ve got someone hooked, and now it’s time to play with them. Instead, I mostly feel nervous.

What’s interesting to me is that when we are submerged in a Lifestyle setting, for example, spending a week on a Lifestyle cruise or resort, I don’t feel nervous at all. I feel electricity with others, and I act on it. I flirt and love on people without any fear, guilt or tension.

The best story I can make up for the discrepancy here is that there are rules at play in Vanilla world that are hard to shake when stepping into a Lifestyle setting. Even if it’s okay for me to flirt with strangers, both by my own moral standards and the rules governing my own relationship, it is decidedly not okay at a societal level. Notice that, in my dream, it wasn’t just fear of betraying Misha that had me feeling guilty, it was also, and substantially, the guilt of “leading on” this other man. What’s that about? It is true, I feel, that when I flirt in Vanilla world, there is this underlying uncertainty of whether or not it will lead anywhere. That uncertainty, perhaps, contributes to the excitement of flirting. Indeed, that uncertainty is still there in swing settings.

The difference, I think, is that in Vanilla world, there are people who are not “supposed” to flirt, namely, committed people. “Supposed” typically implies shame. Just like committed people are not “supposed” to dress slutty (or so they tell me and my husband all the time), committed people should feel ashamed of flirting. And it is this shame, this construct, that seeps through every interaction in Vanilla world. An uncommitted person can flirt with a committed person, but the committed person is supposed to shut this down to indicate that they are committed, as if this serves some unspoken commitment to the uncommitted person. What utter nonsense.

At breakfast, we discussed this dynamic and how, for both of us, we need permission to see reality clearly. It doesn’t protect us to not notice electricity that excites us, it numbs us to the very feelings we entered the Lifestyle to be able to feel again. It doesn’t help our game to be nervous instead of confidently flirting with everyone around us, it holds us back. We want to be able to pursue our sexual wants. That is the point of the Lifestyle. So that means we each need to intentionally shed (some more) the norms of Vanilla world. Not only are we giving ourselves and one another explicit permission to flirt with anyone, we’ve agreed to help each other notice when other people are into us, so we can enjoy it as we deserve.

So much of being in the Lifestyle is a process of unlearning. Isn’t that also true for life? What a gift the Lifestyle gives us: the bravery and incentive to continuously shed old programs, to embrace our true selves, with the reward being sexy sex!